


The Exchange

by alreynolds13



Category: The Walking Dead (TV)
Genre: Desk Sex, Explicit Language, Explicit Sexual Content, F/M, Hot Sex, Sex, Sexual Content, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2016-11-23
Updated: 2017-05-01
Packaged: 2018-09-01 14:54:17
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 8,310
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8628637
Author URL: https://archiveofourown.org/users/alreynolds13/pseuds/alreynolds13
Summary: What would've happened if Maggie and Sasha really were in that closet in episode 7x05? How would you have intervened? (Simon x you smut)





	1. Chapter 1

**Author's Note:**

> Disclaimer: I know, I know, this isn't a Negan story. However, please be kind. If Simon isn't someone you're interested in, that's fine. But, as a fanfiction writer, the one thing I love is that I can write about whichever character that I want to. And damn, did I want to write a little Simon.  
> ~ ~ ~
> 
> Okay, so after watching 7x05, I had this random thought. What if Maggie and Sasha really were in that closet, and Jesus hadn’t moved them? And what if we added in a “you” character who already had a secret crush on Simon? How would “you” react to the situation...and where would it lead ;)
> 
> **NOTE: All I know about Simon is what we’ve seen in the show (since his character isn’t in the comics). Therefore, I had to take some liberties with his personality, and imagine how I thought he might act. Until we see more of him, it’s hard to fully know what is considered “canon” for him, so bear with me in this. With that being said, enjoy :) **

You were standing in the front entryway of Gregory’s house, along with Jesus and a few other members of the community. However, you were vastly outnumbered by the Saviors, who filled the usually large-seeming space, their serious expressions and weapons making you feel small and insignificant. 

Gregory was currently inside his office with the door closed…and _he_ was in there, as well. 

You had been Gregory’s housekeeper for months now, so you should probably feel some sort of loyalty towards him, seeing as how he was the leader of Hilltop and all. But, if you were being honest, Gregory was a real douche. He was condescending to everyone, and he never thanked you for your hard work. Well, unless being constantly looked up and down salaciously and called inferior nicknames such as “honey” could be considered a thank you. 

Now, Simon, on the other hand… _there_ was a real man. It was your dirty little secret that you had it pretty bad for Negan’s right-hand man. Every time he jumped out of that big, blue pickup truck, you felt your breathing accelerate in excitement. He wasn’t handsome in the stereotypical way that had been revered by post-apocalyptic societal standards. His hairline was receding, and he had a handlebar mustache that would’ve been humorous-looking on a less intimidating man. But there was just _something_ about him that made your thighs clench and clit pulse every time you saw him. 

Maybe what you found so attractive was the way he carried himself, all self-assured and full of confidence. Or maybe it was the way his arms bulged in that button-down shirt, giving just a taste of the lean, corded muscles that were hiding underneath. Heck, maybe it was even the way he had Gregory cowering before him with every visit…the way he gruffly told him to kneel at his feet…which caused you to then imagine your own knees hitting the hard floor, so that you could unbuckle his pants and….

You were distracted from your internal fantasies by the study door opening. Gregory came out first, with Simon following a few steps behind. Your breath caught in your throat when Gregory made a beeline for the closet where Maggie and Sasha were hidden. Glancing at Jesus, you saw panic and helplessness cross his face. Everything seemed to stall, as if it were happening in slow motion. And when Gregory’s hand reached out for the closet doorknob, you felt yourself take a step forward, mouth opening without you even fully processing what you were about to do.

“Wait.”

Gregory froze, his head turning and eyes looking at you, both confusion and annoyance crossing his features. But you weren’t really paying attention to him, because Simon had also turned his head, and his gaze was fixed on you, as if unsure how to react to your interruption. 

Realizing that you needed to get him away from the closet, before Gregory went through with opening the door, you nodded at Simon and hurriedly stated, “I need to speak with you…alone.” 

Surprise widened Simon’s eyes slightly, his lips pursing thoughtfully before he nodded. Lifting his arm back in the direction of Gregory’s open office door, he announced, “Well, alright then. After you, darlin’.”

Turning, you caught Jesus’ gaze, his expression questioning, but there was no way for you to respond without seeming suspicious. Walking across the foyer, you entered the study and walked over to stand in front of the large, mahogany desk. Shifting nervously, you watched as Simon closed the door behind him, then took a couple steps into the room. 

He stopped a few feet away from you and cocked his head curiously before saying, “So, girlie, what was so important that you had to interrupt?”

Shit. You hadn’t really thought this far ahead. Searching your brain frantically, you tried to think of a plausible excuse for this “meeting”. 

“I, uh…there’s something you should probably know about.” 

“I’m all ears, sweetheart,” he replied. 

You tried not to blush at his endearment. While Gregory’s pet names always sounded creepy and slimy, Simon calling you “sweetheart” and “darlin’” sounded endearing…and even sexy.

Deciding on what was hopefully a plausible explanation, you shifted your eyes down to the floor and divulged, “Gregory has some supplies that he hasn’t been telling you about. He, uh…he has a whole cellar full of alcohol. Boxes and boxes of it. Scotch, mainly, but I think there’s some gin and whiskey in there, as well.” 

When there was no immediate response, you lifted your gaze and saw that Simon was looking at you, almost scrutinizing in his perusal of your face, as if he could discover all your secrets if he stared hard enough. For the first time ever, you had his full and undivided attention...and your body’s traitorous response was to blush. The heat that flared on your cheeks had to be apparent, and you swore that Simon’s lips twitched upwards briefly on one side, as if in amusement. 

Taking a step closer to you, he hooked a thumb in his belt loop and drawled, “Now, why would you tell me that, hmm? What would make you wanna sell out your pansy of a leader? Because I can’t imagine that you’re telling me this just out of the goodness of your heart.”

Much as you wanted to come up with some elaborate excuse, one that would quickly get him out of the study and away from Hilltop, you realized that this situation could also go an entirely different route. That this could be your one and only chance to make all your hidden fantasies and secret lust a reality. You could get the satisfaction you had been craving, Maggie and Sasha would remain safe, and Gregory would take a hit to his pride with all the liquor gone. Win-win all around.

Gathering some courage, you replied, “I was hoping that in exchange for that information, you might give me something I’ve been wanting for a while now.” 

Curiosity lit up Simon’s eyes, and he chuckled before cocking one hip and taunting, “An exchange, you say? Well fuck, sweetheart. Tell me what it is that you want, and we’ll see if we can’t strike a deal.” 

You swallowed nervously before squaring your shoulders, looking him right in the eye, and saying, “What I want…is you. Right here, right now. One hell of an orgasm in exchange for all of Gregory’s liquor. That sound like a fair trade to you?”

From the way his mouth silently parted in surprise, you could tell that he hadn’t been expecting such an offer. Suddenly, you felt self-conscious. What if he wasn’t interested? What if he laughed in your face and walked out? 

You were about to backtrack and try to turn it all into some big joke, when you saw his eyes finally leave your face. They trailed down over your body, which was modestly covered in a navy-blue t-shirt and jeans, before slowly scanning back up again. When his gaze connected back with your own, he had a fiery glint in his eyes, and a smirk slowly spread across his face. 

“Darlin’, I do believe that’s the best god damn offer I’ve ever received.” Flickering his eyes down over your body again, he licked his lips and drawled, “How about you go ahead and show me what kind of high-quality goods I’m dealing with here.” 

Arousal flooded you at his words, at the fact that the offer had worked…that he wanted you, too. Hands trembled slightly as you reached down and grasped the edge of your shirt, pulling it up and over your head in one smooth motion. Thank god you had put on a clean bra today, this one a soft peach color that complimented your skin quite nicely. You unbuttoned your jeans and pushed them down your hips with a wiggle before kicking both them and your sneakers off, leaving you in a pair of light pink panties. The underwear didn’t exactly match the bra, but hey, you hadn’t exactly expected to fuck your apocalyptic crush when pulling them on this morning. 

Simon’s eyes were fixated on your body, and he gave a breathy, “Fuck,” before he reached up and started undoing the row of buttons on the front of his tan button-down. You watched greedily as his chest was revealed. He pulled the shirt free, shrugging it off his shoulders, before then pulling his thin, white undershirt up over his head. 

You almost stumbled at the sight of him naked from the waist up. _Jesus fuck, he’s ripped!_ You had guessed that he was in shape, but you had no idea that he was hiding such a fine physique. His biceps bulged as he started undoing his belt, his chest muscles and six pac abs flexing underneath a layer of dark hair. He was so strong and masculine that you almost forgot to breathe…and you hadn’t even seen his cock, yet. 

He walked towards you, belt undone but pants still on, his arm reaching out and wrapping around your waist to pull you in against him. Your palm collided with his warm chest, and you shivered as the soft hair on his abs teased your sensitive stomach. You tilted your head up towards him just in time to meet his lips with your own. You had never kissed a man with a mustache before, and the sensation was a bit foreign, but not unpleasant. His tongue danced with yours, and you gave a soft moan when he gently captured your bottom lip between his teeth. 

He reached down and cupped his hand over the curve of your ass before murmuring against your lips, “Yep, I’d say that you’re by far the finest quality of woman I ever have seen…and felt.” With that, his hand gave a firm squeeze, and you pressed closer into him, giving a hum of pleasure as you ran the hand laying on his chest down his taut stomach and over the front of his pants.

“Feels like you’ve got some high-quality goods, yourself,” you purred, cupping his hard dick through the fabric.

He rewarded you with a groan, hand coming up to grab your wrist and lift it away from his dick, while he spun you away from him to face the desk. You felt his hands unhook the clasp of your bra, brushing the straps down your arms and flinging it across the room. You gave a moan of appreciation when his big, warm hands wrapped around your torso and cupped your breasts, the nipples instantly hardening for him. He rolled the swollen nubs between his fingertips, his lips and teeth nipping at the back of your shoulder. 

“Fuck,” he rasped. “Much as I’d like to spend all day like this, if I don’t get back out there soon, they’re going to think something is wrong.” 

You smiled at the tone of his voice. He actually sounded rueful that he couldn’t stay in here with you, which gave you some hope that maybe this could be more than a one-time thing. 

“There’s always next time,” you teased. “Right now, I just want you to fuck me against Gregory’s desk and make me scream.” 

He gave a strangled moan, and a second later you felt his hands leave your breasts, trail down over your sides, and hook in the sides of your underwear. He slowly pulled the panties down your legs, bending over to help you step out of them. You gasped when he rubbed his face up the back of your thigh before gently biting your left ass check. You were pretty sure you’d have a mark from that, and the thought sent a fresh rush of arousal between your thighs. 

The sound of Simon’s pants unzippering gave you a quick jolt of awareness, and you tried to back up, which was impossible since you were pressed between a hard desk and an even harder man.

“Condoms,” you stated, your brain not quite able to form coherent sentences at the moment. 

“What?” he huskily replied. Apparently, you weren’t the only one who wasn’t at full cognitive capacity.

“There’s condoms in Gregory’s desk,” you urged. Much as you wanted him to just dive right on in, that would be an irresponsible move on your part. 

You were grateful when Simon backed up a step, giving you room to move around the side of the desk. You quickly opened the middle drawer where Gregory kept a box of condoms. You had no clue why he had them, seeing as how it was unlikely anyone wanted to sleep with someone so distasteful. But, you had found them once while organizing his desk, so it was about time someone used them. 

Grabbing one out of the box, you turned back to Simon, and promptly felt a throb of heat rush down your spine and settle on your clit. He had taken off his pants while you retrieved the condom, and now stood unabashedly naked in front of you. He had long, muscular thighs that were covered in a sprinkling of dark hair. But it was what was between those thighs that held your attention. 

His cock jutted straight out from his body, long and thick and hard. He wasn’t intimidatingly large, but you were probably going to feel the residual ache from taking in such a well-proportioned cock for days to come. Rounding the desk, you tore open the corner of the condom wrapper. Before you could pull it out, he reached out and plucked it from your grasp. 

“Darlin’, if I let you touch my dick now, this’ll be all over before we’ve even begun.”

You smirked at his words, proud to see that his eyes couldn’t stop trailing over your body, couldn’t stop taking in your curves. It had been way too long since you felt confident and sexy, but standing there naked in front of Simon, you felt just that. 

You walked back over to the front of the desk, bending over and bracing your hands on the cool, flat surface. You slowly rolled your hips from side to side while looking back over your shoulder and purring, “Ready when you are.”

He paused, almost as if he was taking you in and savoring the moment. Then, he confidently strode up behind you, his large, warm body blanketing yours. He inserted a still-booted foot between your legs and pushed your feet wider, spreading you open before him. Rough, calloused fingertips traced down your spine, causing you to shiver and gasp. His other hand curved around your hip, coasting over your stomach and through soft pubic hair to cup your mound. You whimpered when his fingers parted your sopping folds, two of the thick digits entering you slowly, as if to test your readiness.

“Shit, sweetheart, you’re already soaked,” he groaned, starting to pump his fingers in and out of you in a slow, unhurried rhythm.

Mewling, you arched back into him and panted, “Simon, please, fuck me…make me yours.” 

You felt his warm breath puff over your shoulder before he trailed his tongue up the side of your throat and whispered, “Oh, trust me, darlin’. You are most certainly mine now.”

With that, he removed his fingers, positioned his cock at your entrance, and started to push inside. You whimpered at the sensation of your walls stretching as you took a man inside for the first time in way too long. Hell, you were pretty sure that you had never taken in a cock quite this big. Nails dug into smooth wood as your world dwindled down to Simon’s mouth on your neck, his hands on your flesh, and his dick sinking deep inside you. 

“Fuck,” you breathed as he bottomed out, his balls warm against your ass. 

“You ready for that one hell of an orgasm, darlin’?” he taunted, his own voice breathy and low. 

“Yes! God, yes!” you begged, giving a whimper of gratitude when he pulled out of you slowly, before pushing back in. 

His right hand snaked around your waist, lowering to center on your clit. You keened as his fingers started up a precise, circular rhythm that was perfectly timed to the pace of his thrusts. His left hand came down over top your own, anchoring it to the desk, the palm and fingers so large that it completely dwarfed yours. The contrast between your bodies ramped up your desire; his body large and hard where yours was small and soft. His, rough and full of sharp edges, where yours was pliant and curved. 

You started to feel the coil of pleasure tighten as he continued to fuck you, both his cock and fingers moving at a rhythm that was guaranteed to make you come in record time. You bowed your head with a moan when he trailed his lips over the curve of your shoulder, his hips snapping against you sharply as he bit down on your oversensitized flesh. The fact that he would now leave behind two bite marks, as reminders of this moment and his possession, caused you to tremble and moan loudly. 

You raised your head so that it was pressed back into his throat, his rough pants and deep grunts playing in your ear like a symphony. You were so close that you could almost taste it, your body ramped up to the edge of pleasure, only one small push away from flying over the edge. 

He must’ve been able to tell, because he gave you that push in the form of his low, husky voice. “That’s it, darlin’. Come all over my cock; let them all hear you scream.” 

As if his words facilitated the response, your orgasm smashed into you like a tidal wave. Your body dissolved into shockwaves of pleasure as you rode out the most intense orgasm of your entire life. Vision blurred and loud cries fell from your lips as you shivered and shook and came all over Simon’s cock. You heard him groan loudly behind you, giving a choked, “Fuck!” as he reached his own peak.

You both stood there for a minute, panting heavily as your heart rates slowly returned to normal. Your body gave a residual shudder when he moved his left hand up over your arm and shoulder before trailing it down the left side of your torso. His other hand was rubbing soft circles on your stomach, and it was almost as if he didn’t want to stop touching you. Didn’t want to let you go. 

But, sadly, the moment couldn’t last forever, and too soon he stepped back from you. Turning, you leaned back against the desk, the two of you scanning the other’s bodies, drinking each other in. He had a sheen of sweat across his chest that made your mouth water and clit twitch, as if your body was already forgetting that it just finished having an earth-shattering orgasm. 

You both smiled at each other silently before reaching for your clothes. You grabbed the pink panties off the floor and pulled them on, before walking over to where he had tossed your bra onto a nearby chair. When you turned around, he was standing there with his pants pulled up but not buckled, holding out your t-shirt. You walked up to him and took it from his grasp, slowly pulling it back down over your head while he watched. You licked your lips and gazed up at him, wanting to say something, to ask if this would happen again. However, you didn’t want to risk ruining the moment, so you turned to pick up your jeans, instead, while he pulled on his undershirt and button-down. 

When you were both fully dressed, he gestured for you to proceed him out of the study. You opened the door and stepped out into the foyer, and it was almost as if you had completely forgotten just how many people were waiting out there. Heat flared on your cheeks at the sight of Gregory, Jesus, and every single Savior staring at you with various expressions ranging from shock to smirks. Walking back to where you had previously been standing, you glanced over at Jesus, who was looking at you bewildered, as if unsure what to think of the situation. 

Simon, on the other hand, had a huge smile on his face as he walked up to Gregory and announced, “Well, I think that about concludes our visit.”

Turning to his men, he ordered, “Go to the cellar and bring me all the boxes of liquor you can find. Turns out ol’ Gregory here has been holding out on us.”

You watched in satisfaction as Gregory sputtered and looked panicked as the group of men walked past him to carry out Simon’s orders. 

After the Saviors had brought up all the boxes and taken them out to load into the truck, Simon put his hand in the air, as if he had almost forgotten something important.

“Oh, one last thing, Gregory.”

Walking up and putting his hand on Gregory’s shoulder, Simon gave a happy grin and said, “Can I just get a kneel out of you?”

“Excuse me?” Gregory asked, seemingly confused by the request, as if he were still trying to process the fact that all his liquor was now gone. 

Simon moved his face closer, grin disappearing as he stared dominatingly at Gregory and ordered, “Kneel.” 

You felt way more satisfaction than you were willing to admit when Gregory nodded and slowly lowered himself to the floor. And you felt a tingle of arousal go up your spine when Simon bent over so that his face was right in front of Gregory’s, providing you with a spectacular view of his taut, muscular ass. 

Giving a slow smile, Simon praised, “That’s a solid kneel, Gregory.” Patting him on the head, as if he were a loyal dog, Simon added, “You remember that for next time.”

He then turned and started for the door. He caught your gaze on the way past, giving you a wink and smirk before he headed out the door. When Gregory had risen back to his feet, his gaze fixed on you, anger palpable in his silent glare. However, you found that you honestly didn’t give a shit what he thought. Nothing could ruin the post-orgasmic high you were currently riding. And even better than that, you were pretty sure that it wouldn’t be the last time you got to make such a pleasurable deal with Simon. You knew a lot of Gregory’s secrets, from being his housekeeper, and you would gladly give them up to Simon, if it meant feeling his cock inside you again. 

Smiling, you turned and walked away from Gregory, your body already tingling with excitement at the thought of Simon’s next visit.


	2. S is for Secret

**Summary for the Chapter:**

> A sequel chapter, where Simon revisits you at Hilltop.

**Notes for the Chapter:**

> Sooo I wasn't planning on making this more than a one shot, but I joined a Simon fic challenge on Tumblr, where everyone took a letter of the alphabet and made a Simon fic from it. I got the prompt S is for Secret, and I couldn't help but make a sequel chapter to "The Exchange", so I hope y'all enjoy it!

Excitement flowed through your body, the moment you heard the vehicles pull up outside. That noise could only mean one thing: The Saviors were here to collect their weekly goods.

Your thoughts over the last seven days had been consumed with memories of the last time Simon, and his men, had come to Hilltop. In fact, you hadn’t even been able to look at Gregory’s desk without getting a rush of dampness between your thighs. 

And now, he was back. 

You had been in the middle of serving Gregory lunch, and internally smiled at the way the color drained from his face, when he realized who had arrived. He had nervously cleared his throat and adjusted his suit, brushing off imaginary lint before ordering you to round up the rest of his staff and wait in the front entryway for further instructions.

You hoped that Maggie, and her friends from Alexandria, were alerted in time to find a decent hiding spot, since their discovery would probably cause a shit storm of rage from Negan. However, your thoughts only drifted to them for a few seconds, before getting distracted by the fact that you were going to see Simon again. You wondered if he had thought of you the way you had thought of him…if he missed your body the way you had already began to miss and crave his. 

A few seconds later, the front door opened, and a group of Saviors filed into the room, Simon sauntering in behind them. His hands gripped the front of his belt as he surveyed the group of people in front of him. You gave a slight gasp as his eyes locked with yours, the left side of his mustache twitching slightly upwards as he gave you a quick smirk before turning his attention back to his men. 

_Damn, he looks good,_ you thought. He had on a button-down shirt, similar to the one he had worn last week, except this one was a light grey color. The first button was undone, showing the top of his white undershirt, and allowing for just a peek of dark chest hair. Matching grey cargo pants were tightly molded to his muscular thighs and ass, and you felt beads of sweat start to form on the back of your neck, as the temperature in the room seemed to escalate about a thousand degrees. 

You watched, in fascination, as he instantly put Gregory off balance with his words. It was almost impossible to keep the grin off your face when Gregory tried to get on Simon’s good side by offering him a drink in his office, only to be rebutted in favor of Simon ordering his men to go through the large house and collect what was owed them. He then ordered Gregory to take him to Dr. Carson, and you watched, a bit disappointed, as the two men left the house without another word. 

Your disappointment was short-lived when, less than ten minutes later, Simon returned, alone. Seeing that his men were all either keeping watch over the community, or busy loading up the needed goods, he gave a nod of approval…and turned his attention on you. 

Caught in his gaze, you felt your heart rate increase as he walked over to where you were standing. Looking down at you, he drawled, “You need to talk to me this time, too, darlin’?”

Knowing that the lingering Saviors and rest of the house staff were watching, you prayed you weren’t blushing as you looked up at Simon, and steadily replied, “I do.” 

Stepping back, he motioned for his men to carry on with their duties, then waited for you to kick shaky legs into action and cross the room, before following you into Gregory’s office. You almost stumbled with excitement when you heard him not only close the door, but lock it, as well. 

There was a strong sense of déjà vu, as you stared at each other from a distance of a few feet. This was exactly where the two of you had been standing a week ago, when you first entered Gregory’s office together. Except, this time, you knew what Simon looked like naked, and you also knew that he had the ability to make you come harder than any man before him. 

Putting on a wide grin and resting his hands on his hips, he asked, “Well, darlin’, whataya got for me this time?” 

_Whatever you want, whenever you want it,_ you thought. Giving yourself a mental slap, and a reminder that he was currently asking for information, not to fuck, you tried to push away the X-rated thoughts, but were only semi-successful. 

“I’ve got plenty of intel on Gregory for you. Only problem is, I keep giving away all of his secret stashes, and he might decide I’m more trouble than I’m worth here.” 

Your words were nothing but the truth, and aired your main worry in this little arrangement with Simon. Gregory had obviously been pissed last time, and had made sure to give you the grimiest, most labor-intensive cleaning jobs he could find, in retaliation. The man was such a snake, that it wouldn’t surprise you if he found a way to “accidentally” get you killed, if you continued to go against him. 

Simon looked at you thoughtfully. Surprisingly, he seemed to be considering your words, rather than just brushing off your safety, which caused a warm, tingly feeling to erupt in your chest. 

Walking further into the room, he said, “How about you let me take care of Gregory. He won’t dare do shit if he knows I have my eye on him.” 

You relaxed at his words. Even though this was only your second one-on-one interaction with him, you believed Simon, and trusted him to keep you safe. If there was one thing you knew for sure about the Saviors, it was that they kept their word. Which was more than you could say for Gregory. 

Nodding in agreement, you gave a sly smile, and replied, “Well, in that case, perhaps you’d like to know about Gregory’s guns.”

Simon’s eyebrows raised at your words, and he drawled, “Go on.” 

Lifting a hand and pointing your thumb over your right shoulder, in the direction of Gregory’s office closet, you divulged, “They’re in there. He’s got a pistol and two shotguns wrapped up in a poncho in the back of the closet, on the left. The day I found them, he told me they were for our protection, but you and I both know that Gregory wouldn’t have the guts to use those on anyone, unless it was for his own personal benefit.”

Simon gave a sarcastic huff of agreement, before walking across the room, towards the closet. His hand lightly grazed your hip as he passed by, causing a shiver to go up your spine. You watched as he opened the closet door and bent down, reaching into the back corner. Leaning a hip against Gregory’s desk, you stared lustfully at his taut ass, as he gathered up the poncho-wrapped guns. Straightening back up, he turned around and uncovered the guns with a low whistle.

“Jackpot,” he announced with a grin, and you couldn’t help but smile back at him. 

He walked over and set the guns down on one of the brown chairs beside the fireplace, before turning and coming closer, so that he was right in front of you.

“Thanks for the info, sweetheart. Now, I think it’s only fair that I offer you something in return.”

Smile still in place, you tried not to sound overly eager when you asked, “What’s your offer?”

Tilting his head to the side, he looked you up and down while considering his next words. “Well, since I don’t have any verbal information that would be valuable to you…how about I put my mouth to good use in another way,” he offered with a wink.

At first, you were confused by his words, but then, his meaning hit you over the head, almost causing you to topple to the floor. _He wants to…oh fuck…oh fuckkkk._

It took a few deep breaths before you were able to respond, your voice already needy with want.

“Yes, please.” 

You saw his eyes visibly darken, the pupils dilating in response to your breathless words. He reached out and fingered the bottom of your shirt, and you obeyed his silent request by lifting your arms above your head. He immediately pulled the shirt up and over your head, leaving you in just your bra, which was black and lace-trimmed. You were only slightly embarrassed to admit that you had purposely worn your nicest bra today, in hopes that the Saviors would visit, and lead to the exact situation you were currently in. 

“My turn?” you asked, looking up at him with eyes that were probably as lust-blown as his own. 

When he nodded, you reached out and started undoing the buttons down the front of his shirt, biting your lip when he shrugged the shirt off his shoulders, showcasing his bulging biceps and corded forearms. You reached for the hem of his undershirt, but were only able to push it up to his pecs before you got distracted by his bare chest. 

Simon took over, pulling the undershirt up over his head and tossing it off to the side, as you reached out and laid your palms on his warm chest. Finally getting the chance to explore, you licked your lips as fingers traced over taut abs covered by a dusting of dark hair. He gave a soft groan when your thumbs traced up over his nipples, and you grinned. You felt so powerful in this moment, able to make such a large, strong man react to you in this way. You could stand here and touch him like this all day, if he let you. Simon, however, had other plans.

He reached down for the button on your jeans, undoing it and sliding down your zipper, before bending forward so that he could slide the fabric down your legs. You kicked off the fabric, and were pleased to see that he was staring at your body in awe. You had put on matching black panties, and you knew for a fact that you looked pretty damn good in them. 

“Je-sus,” he whispered, drinking in the sight of you, in the delicate lace. 

“It’s all for you,” you throatily replied. 

A muscle started to tick in the left side of his jaw at your words, and he huskily commanded, “Take them off.” 

Without hesitating, you reached back and unhooked your bra, sliding the straps down your arms and letting the cups fall away from your breasts. Simon’s eyes practically burned a trail across your flesh, as he took in your curves, and the muscles in his arms flexed, as if he were holding himself back from reaching out and touching you. 

Hooking your thumbs in the sides of the panties, you slowly slid them down your hips and thighs, until they dropped to the ground on their own. Standing there, in front of Simon, you felt like a goddess. Any self-consciousness or fear of rejection was annihilated by the look of pure lust and awe on his face. The fact that such a handsome and powerful man was captivated by your beauty was one of the biggest turn-ons you could imagine, and sky-rocketed your confidence and boldness so that you didn’t hesitate to walk up to him and go up on your tiptoes, head tilted back, as you searched out his lips with your own. 

The kiss was full of passion, tongues dancing against one another as you quickly relearned each other’s mouths with teasing nips and languid thrusts. You were both breathing heavily when Simon finally pulled back, one warm hand resting in the middle of your back, while the other gripped your hip. 

Reluctantly allowing Simon to take a step back, he reached down and wrapped his hand around your own, leading you around the desk. You could see how his erection strained against the front of his pants, and it was so tempting to reach out and touch him. However, the thought of his mouth on your pussy stayed your hand, although you promised yourself that you would also feel his cock, one way or another, before leaving this room. 

Pushing back the desk chair, Simon gave a slight tug on your hand, to bring you forward. “Come here, sweetheart.” 

Giving a small shudder at the endearment, you walked forward, so that you were standing between him and the desk. His large hands came down on your hips, lifting you up onto the large structure, the wood a cool contrast against your bare ass and overheated cunt. 

Pulling the chair back and sitting down, so that his face was now level with your hips, Simon ran his hands down the outside of your thighs, before placing them on your knees and looking up at you. 

Holding eye contact, he used his grip on your knees to slowly pull your legs apart. You gasped, overwhelmed by the intensity in his gaze, as he spread you out before him, until your thighs were opened as far as they could go. 

It was only then that his eyes trailed downward, taking in your dripping, spread cunt. With anyone else, being so open and vulnerable would’ve been embarrassing, but under Simon’s gaze, all you could do was tremble and burn with anticipation. 

You watched him move his head forward, as if in slow motion, your thighs muscles tensing with excitement. You knew that once he got his mouth on you, you’d be ruined for any other man. However, you didn’t care, because the road to damnation had never felt so delicious. 

The first touch of his mouth on your pussy almost sent you arching off the desk. Simon quickly anchored down your hips with his hands, his arms wrapped around your thighs in a way that kept you from closing them against the sensations. 

Crying out, you let your upper body fall back against the cool wood, shoving papers out of the way uncaringly. Your nails gripped at the shiny wood, and you stared up at the ceiling, mouth hanging open, as Simon’s tongue took you to heaven and back. 

His tongue licked up your slit from ass to clit, before he zeroed in on your clit with the type of precision that showcased just how well he knew his way around a woman. And when he groaned against you, the vibrations seemed to flow into your cunt and throughout your entire body, causing you to twist on the desk in ecstasy. 

Lifting your head, you let out loud moan at the sight of his head between your thighs, face buried in your pussy. You couldn’t see exactly what he was doing, but the obscene sounds his mouth was making against your wetness, combined with the feel of his tongue and lips, made your thighs quiver and hips twitch under his grip. 

And, on top of all that, you were introduced to an entirely new sensation: his mustache. It tickled your clit in just the right way, creating extra friction which pushed your pleasure to the next level, to the point where the stimulations were almost painfully overwhelming. 

The coil in your stomach wound tighter, and you quickly found yourself at the brink of coming. You wanted to hold off, to make it last, but the pleasure was too much. Between the delicious way he was restraining your lower body, his mouth working its magic between your thighs, and the feel of another groan vibrating against your cunt, you had no choice but to give over to your orgasm. It rolled through you like a crescendo, starting at your clit and expanding throughout your entire body, until even your fingertips tingled with the pleasure. You arched your back, as best you could with Simon’s strong hands holding you down, riding out the waves of pleasure, as you cried out his name desperately and stared sightlessly at the ceiling. 

Only when your body went limp, except for the tiny aftershocks causing the muscles in your thighs and waist to jerk randomly, did Simon pull back. Looking down at him, you whimpered at the sight of your wetness coating the lower half of his face, even his mustache shining with evidence of your orgasm. You almost couldn’t believe it when sparks of fresh desire traveled through your body at the sight of him licking your arousal off his lips, before rubbing the rest onto the back of his hand. 

Struggling to push yourself up on trembling arms, you managed to resume your previous sitting position, just in time to see Simon reach down and start unzipping his pants. Taking out his hard cock, you watched as he gripped himself and started slowly pumping up and down, causing precum to leak out the tip.

“You ready for me, darlin’, or should I take care of myself this time?” 

The fact that he would even offer to jerk himself off, and let you rest, was more thoughtfulness than you would ever expect to receive from such a high-ranking member of the Saviors. Although, it was ridiculous for him to think that you would pass up the chance to feel his cock inside you. Just watching him sent fresh wetness between your thighs and caused your pussy to ache, as his hand stroked and squeezed his thick dick, while his abs and biceps flexed with each downward stroke. 

“Get a condom,” you answered, surprising yourself at the way the words came out, more a command than a suggestion.

“Thank fuck,” Simon breathed, reaching over and opening the drawer that he knew, thanks to last time, held the pack of condoms. You watched, mesmerized, as he opened the packet and rolled the rubber down his long cock, before looking up at you expectantly.

Praying you could do this gracefully, you slid off the edge of the desk and down onto Simon’s lap, successfully spreading your thighs on either side of his and positioning your dripping cunt over his dick. 

Reaching down, you wrapped one hand around his thick cock and lined him up with your entrance, while he moaned and encouraged, “Yes, that’s it, sweetheart. Put it in.” 

Sinking down onto him, slowly, you closed your eyes and threw back your head as his cock opened you up, stretching your walls in order to accommodate his girth and length. He felt so deep in this position, and you both groaned in unison when he was fully seated inside you. 

Over the past week, part of you had wondered if perhaps your memories exaggerated how good sex with Simon was. That maybe his cock didn’t really feel as good as you thought. 

You quickly realized that you hadn’t exaggerated at all, and that Simon’s cock inside you was the best sensation you had ever felt. Well…that or his mouth on your pussy; at this point, it was impossible to decide. 

Swirling your hips in a circular motion, you whimpered at the full pressure of his cock stuffing you to the brink. Growling in response, Simon’s hands gripped your hips, encouraging you to grind against him again. 

Using your knees for leverage, you lifted yourself up his cock a few inches before sliding back down, twisting your hips as you did so. The groan you got in reward caused a smile to tip your lips, and you did it again, starting a slow up and down rhythm, swirling your hips with each stroke, until Simon was moaning almost continuously and staring down at where your bodies were joined, as if hypnotized. 

Simon’s pants were still on, and the material rubbed against your sensitive thighs. It should’ve been irritating, but instead, it heightened your pleasure. He also still had his gun holster strapped around his hips, and the sight caused your clit to throb. Thoughts of him pulling out the gun, running the metal along your exposed flesh, made you whimper and move your hips faster. 

You felt Simon’s hands run up your waist and move around your back, leaving no inch of you untouched. When the large palms covered your breasts, you mewled and arched your back, offering them to him. Roughly pinching the nipples between his fingers, he delighted in your pained gasp, before leaning forward and soothing the ache with his tongue. 

Your movements became jerky and off-rhythm as his mouth painted your breasts with nips and licks, before he moved up over your chest and to your neck. Moving your head back, you gave him full access to your throat, continuing to work your hips over his dick as best you could while luxuriating in the feel of his hands once more at your breasts and his mouth sucking marks, like a necklace, into your skin. 

Instead of continuing to move up and down, you pushed down into him with your hips, until he was seated so deep that you could feel the rough material of his pants pressing into your ass. You then started rocking your hips back and forth, grinding down on him in a way that rubbed your clit against his pelvic bone, and made his dick hit just the right spot inside you. 

“Fuck, Simon, I can’t…I’m gonna…” 

“Do it,” he ordered, bucking his hips up into you, causing you to cry out. 

He wrapped one of his hands tightly in your hair, to hold you steady. Sinking his teeth into your shoulder, at the same moment that he gave another quick thrust up into you, was all it took to send you over the edge. 

Head thrown back, your nails clawed at his shoulders, and your hips ground down into his, as the shudders wracked your body. He groaned as your walls contracted around his cock, and gave a few more quick thrusts before reaching his own orgasm, his body trembling and jerking against yours. 

Gasping for air, your limbs went heavy with exhaustion as you came back down from yet another fantastic orgasm at the hands of Simon. _Well, more like at the mouth and cock of Simon, you thought with a grin._

You both stayed that way for a few long minutes, Simon’s mouth tracing across your shoulders and collarbone, while you ran your hands along his arms, tracing the muscles and loving how they flexed beneath your fingertips. 

Eventually, you both knew that it was time to move, that you had been in here for way longer than was needed. Chances were, the goods had already been loaded into the trucks, and Simon’s men were waiting impatiently for him to stop fucking you and get back to work. 

Crawling off his lap, you turned to look for your underwear, while Simon pulled off the condom and threw it in Gregory’s waste basket, not even bothering to hide it in a tissue. You smirked to yourself at the idea of Gregory seeing the condom, but then quickly sobered up at the thought of how many shitty cleaning jobs he was going to give you in retaliation.

Once you were both fully dressed, Simon walked over to gather up the guns from the chair. Picking up the papers you had earlier shoved onto the floor, you set them back on Gregory’s desk. 

It was then that you noticed the wet spot on the dark wood, and felt a blush heat your cheeks. You were looking around for a rag to wipe it up, when Simon’s voice came from behind you. 

“Leave it,” he ordered.

Turning with a questioning look, you saw him smirk as his eyes trailed down over your body. 

“I want him to find it, and know how it got there. And then, every time he sees me, he won’t be able to fucking forget that I made you come all over his precious desk.” 

Cheeks flushing at his words, you nodded. It wasn’t worth it to ruin Simon’s mood by pointing out that Gregory would just find you and make you clean up the mess yourself, after Simon left. Plus, it was indeed exhilarating to give Gregory this nonverbal ‘fuck you’, even if you would probably more than pay for it in the future. 

Following Simon across the office, he unlocked the door and walked back out into the foyer. Thankfully, most of his men had left, probably to load up into the trucks. Only a select few remained, to keep an eye on Gregory and the other staff. Gregory had an obvious look of disgust on his face, which turned to silent rage when he saw that Simon was holding his guns. It was obvious that he was going to give you holy hell as soon as the Saviors left, and you felt a slight twinge of dread.

You were so focused on how you were going to deal with an irate Gregory over the next week, that you didn’t notice Simon had stopped by the front door, and was looking back at you. 

“Well, you coming or not, darlin’?” he drawled. 

Jerking your gaze to his in surprise, brows furrowed as you realized he was indeed talking to you. 

“I…what?” you stumbled, unwilling to believe that he could really be asking what you had been hoping for.

Smirking at your confusion, he elaborated, “It’s clear that your talents are being wasted here, scrubbing floors and washing windows. Instead, I think we could use you as a valuable asset at The Sanctuary. At least, if that’s what you want.” 

Out of the corner of your eye, you saw Gregory’s mouth drop open slightly, and the rest of the staff also looked shocked, waiting to see how you would reply.

Unable to contain your joy, you gave Simon a mega-watt smile, and happily replied, “Of course I’ll come with you!”

Smiling back at you, Simon jerked his head over his shoulder and said, “Well then, get a move on, sweetheart. We gotta get back before sunset, so we can get this shit to Negan.” 

Head held high, you marched across the foyer, looking over at Gregory and huffing a laugh in his direction as you passed by. 

You followed Simon outside to his truck, where he helped you up into the passenger’s seat. When he started the engine, and turned the truck around, you looked over at him fondly.

“Thank you.” 

Grabbing your hand with his, so that your fingers were intertwined on the seat between you, he laughed, “No, thank you, darlin’. Even with all our supply runs, I never expected to find such a worthwhile treasure to take home with me.” 

You couldn’t wipe the smile off your face, as you drove past the fences of Hilltop and out onto the road. You didn’t look back…not even once.


End file.
